What would seem like folly of ludicrous proportion to most of us is something that happens yearly in the NBA. Teams go out and either extend their current players or sign new ones for ridiculous amounts even by pro sports standards, leaving their cap situations looking more dismal than an Atlanta Hawks playoff guarantee. While many of these contracts seem at least semi-understandable at the time but then give way to ruinous runs of injuries (Terrell Brandon, Penny Hardaway and Grant Hill to name a few), others are head-scratchers from the moment the ink dries.

With the varying level of competence among NBA general mangers, this seems like something that one would expect to happen. The much-maligned Kevin McHale is no stranger to these types of blood-draining pacts, having signed Marko Jaric and Troy Hudson to a combined $70 million USD over a whopping twelve years of mediocrity. Some teams are content to harbor their crippling contracts though, the Wolves being a perfect example.

Where it gets confusing is where the team signs the player to what every analyst, fan and pygmy shrew can recognize is a bad contract and then that team, having clearly undergone some magical stroke of realization, almost immediately attempts to trade the player in question. This scenario usually has disastrous consequences. However, sometimes the team manages to break through with an outstanding turn of fate (or perhaps it merely takes advantage of a general manager with an even worse idea of cap management). Whatever the case, watching extremely intelligent men who are paid millions each year struggle with what often seem to be no-brainer situations is somewhere between hilarious, frustrating and sad.

Why do general mangers engage in this mind-boggling exercise? I’ll be honest with you: I don’t know. I don’t even have a clue. If I had the answers, I’d be sitting in New York sipping a scotch while working the phone lines and saying the name “Eddy Curry” about ten times a minute. Maybe by looking at some places where general managers have faltered, though, we can inch closer to the stupefying truth.

Mired In Manhattan: The Isiah Thomas Story

Isiah Thomas, who became both famous and infamous within the span of about a decade, has had an exceptionally difficult time dealing with Scott Layden’s leftovers. Upon Zeke’s ascension in New York, the Knicks’ payroll was putrid: players like Shandon Anderson and Howard Eisley were making upwards of six million dollars per year and Allan Houston was on a nine-figure deal. Even retreads like Clarence Weatherspoon, who rebounded well for a couple seasons before becoming grossly overweight, were receiving massive paychecks.

So naturally, Isiah Thomas cleared them all out in an effort to acquire players with larger per-year but shorter overall deals while also chipping at other teams’ supplies of draft picks along the way.

Wait a second…

Welcome to 2007. Eddy Curry, Jamal Crawford and Quentin Richardson are all on the books for approximately $25 million this year alone, with none of them expiring until 2010. Each one has a player option in his contract. Stephon Marbury is making a cool twenty million this year while the newly acquired Zach Randolph is only two years into a six-year, $86 million atrocity that the Portland Trailblazers were dying to unload. (If you don’t believe they were, ask Steve Francis, who they’ll be paying about $30 million over the next two seasons to play for a division rival. Apparently this is better than paying Randolph.)

While all of these contracts are horrid, the players attached to them can all play pretty well. Even Malik Rose, who has two more years left at about $7 million per, has a bit left in the tank and is looking like a good enough payment for acquiring David Lee. Where Isiah Thomas has truly failed is in his use of the mid-level exception, a yearly sum awarded to over-the-cap teams that amounts to $5 million.

Isiah Thomas’s two chief mistakes, no matter how often he repeats them, are most evident in these two blunders.

Paying for the playoffs: Remember Jerome Moiso? If you do, this should all make sense to you. If not, that only proves my point even more. Jerome James isn’t much better, a career backup who finished this past season averaging 1.9 points and 1.6 rebounds per game and owns averages of 4.3PPG and 3.3RPG lifetime.

Two summers ago, Isiah Thomas gave him $30 million over five years.

James had an impressive first round series against the Sacramento Kings in 2005, averaging a very solid 17.6PPG and 9.4RPG, but fell off against the Spurs and finished those playoffs with 12.5PPG and 6.8RPG, which are decent numbers but hardly worth being called the highlight of a career. Furthermore, he had just finished a similar contract that had seen him play little better in Seattle. By all accounts, he was a player who was unmotivated and didn’t have a good mental grasp of the game – basically, the exact sort of player who you don’t reward with a big deal.

Overestimating young talent: Some would think Thomas would have learned against the dangerous practice of bidding against himself by summer 2006 but there it came and all of a sudden, Jared Jeffries was a Knick for the same deal awarded to James. While always something of an intriguing player with the Washington Wizards , Jeffries had never really excelled in any one facet of the game. The Knicks hoped he would shore up their defence but since his arrival in the Big Apple, he’s done little but warm the pine.

Having averaged 4.1PPG and 4.3RPG this season, he’s certainly an improvement over James but not much better. Like James, he’s become a bit piece, especially with the pleasant surprise that is Renaldo Balkman.

The common thread between James and Jeffries is not only that they’ve received identically huge contracts (a sure by-product of teams underestimating the value of the exception and therefore blowing it all at once) but that Thomas doesn’t seem particularly attached to either player. It’s common knowledge that any chance to unload James would be a blessing at this point, although no one will take him, and Jeffries’ name has been floated in a couple rumours – from the Knicks’ side. My gut instinct is telling me that if the Knicks indeed do want Ron Artest that badly, the Kings will insist that Jared Jeffries is not the centrepiece of a deal. (Or likely even included at all.)

Odiferous Otis and Orlando’s Ostensibly Offensive Ordeal

Bad as many of Isiah Thomas’s contracts have been, it actually gets worse. One of the NBA’s biggest headlines this summer has been the six-year, $118 million enormity that Orlando’s Otis Smith handed to free-agent forward Rashard Lewis. Without getting into why Lewis is undeserving of that echelon of pay, the reasons being innumerable, let’s look at why Smith handed him that contract and what it means for the team.

Desperation: Is there any worse reason to be handing out a maximum contract? Orlando needed a scorer, everyone had already been re-signed and as a result, Lewis and his agent were able to squeeze the Magic for every last dollar they could.

This impatience cost Orlando a shot at re-signing Darko Milicic, which means that through eliminating an old need, they’ve acquired a new one. The Magic are starving for frontcourt depth, with Dwight Howard only being one man and Tony Battie being well above the average league age. Lewis might be an impressive scorer but when your other forward is Hedo Turkoglu or Pat Garrity, it’s really not very impressive. Let’s hope Lewis enjoys putting up tons of points on what’s looking like a very thin team.

The added cap burden: This obviously isn’t a reason for the contract, unless Otis Smith is a masochist, but it has to be mentioned nonetheless. Lewis is taking up over a quarter of the salary cap and is expected to do so for the remainder of his contract, leaving Orlando in a situation where there aren’t many options in terms of other free agent signings. Coming back to the main theme, no one will dare trade for Lewis now; maybe Orlando doesn’t want to trade him but even so, what if he doesn’t work out or he gets injured? Juwan Howard’s $30 million payout and subsequent loss of talent combined with a heart problem should have made the Magic wary of huge deals.

Ultimately, what this means is that the Magic will have to pay Rashard Lewis almost $16 million this coming season, which is painful as mentioned but looks even worse when it’s converted into an actual dollar figure. I hate to be so cruel to Lewis on his twenty-eighth birthday but age is another factor; that contract won’t expire until he’s almost thirty-four, at which point he’ll likely be little more than a spot-up shooter who’s making $24 million. Allan Houston doesn’t look so bad anymore, does he?

Escape from Oakland

After these tales of gloom, it’s nice to think that maybe a team can free itself from horrible contracts. Just like we all want to atone for our mistakes, surely a general manager can repent for his wrongdoings… right? Absolutely!

The Golden State Warriors , once saddled with the contracts of Jason Richardson ($72 million, six years), Troy Murphy ($54 million, six years) and Mike Dunleavy, Jr. ($45 million, five years) can breathe again. No, the figures for Dunleavy weren’t a typo. Let’s look at what got the Warriors into this mess and how they seemed to emerge from it virtually unscathed.

A desire to keep the core intact: It’s rather odd that a team unable to secure a playoff berth for a decade would be so eager to ensure it would keep its current roster but alas, this was the style of thinking prevalent in Golden State in 2004. Jason Richardson was a rising star who had won the 2002 and 2003 dunk contests and Troy Murphy was looking like an exceptional rebounder. This led to them receiving a combined $124 million over the span of about two days, a pair of moves that some lauded but more disliked.

Richardson and Murphy seemed like a good pairing in some ways. Richardson’s athleticism, a huge asset in terms of his ability to drive, combined with Murphy’s penchant for cleaning up misses was the basis for Golden State’s young nucleus that seemed prime for a playoff run… well, maybe in their minds.

Agent pressure: Dan Fegan was the agent for both Richardson and Murphy at the time of their extensions, and rumour had it that he was pressing extremely hard for something to happen. He cashed in big, giving his clients a lot of money, but one can’t help but think that the Warriors were weak in the negotiations. Regardless of Fegan’s prowess in the war room, what allegedly happened in those sessions is a very strong indictment of Golden State’s management capabilities. It would also explain a lot of the other big contracts that are given every summer.

Finding answers: I didn’t mention Dunleavy’s contract because I can’t think of a single reason why they’d give it to him. Needless to say, the Warriors ended 2005 with three bad contracts attached to players who weren’t effective on defence and weren’t bringing playoff berths to Oakland.

Murphy’s injuries and Dunleavy’s inability to translate to the NBA game made them seemingly impossible to trade, to the point where I once predicted that if the Warriors were unable to dump their bad deals, they’d be mathematically eliminated from playoff contention until 2010. Somehow, though, they stumbled across an offer that was just too good to refuse.

At first, the Pacers/Warriors trade that sent Murphy and Dunleavy along with Ike Diogu to Indiana for Stephen Jackson and Al Harrington (essentially) didn’t seem that bad. Harrington for Murphy had reportedly been in the works and Diogu seemed like a fitting reward for the Pacers to take Dunleavy. Looking back, there’s no question who won that trade. The Warriors made the second round of the playoffs and the Pacers had their worst season since Reggie’s early struggles.

The Richardson trade, to Charlotte for the Brandan Wright pick, was another masterpiece. Golden State dumped a huge contract while gaining extensive salary relief and a top prospect to boot. The Bobcats have so much cap room that they likely don’t care paying Richardson $12 million a season to be their leading scorer so it looks like it benefits both sides.

The Moral of the Story

After all this, you’d think there would be something to lead general managers back down the right path. New York and Orlando are still awash in penned peril while Golden State is looking fantastic, not to mention exciting to watch. What’s the big secret?

Aside from absorbing other teams’ asylum candidates (see: Stephen Jackson), notice where teams are using the aforementioned flawed logic and turn it against them. The Pacers was desperate for both a young post player (Diogu) and wanted a character player (Murphy) so they bit on what’s become a scourge to them. The Bobcats needed a scoring off-guard so they gave up a player teeming with potential to get one.

Taking advantage of weak points, both in player agents and opposing teams, is a good way to get out of bad contracts. Whether there’s a sentimental attachment somewhere, the feeling that no one else is bidding for the player or merely the common-sense realization that a player simply isn’t made from one playoff series, well-planned signings and trades can vanquish many cap-related worries. Of course, if everything were so well-planned, perhaps these monstrosities would never surface at all…

migya wrote:Mullin will show how good he is with the level of contracts he gives to Monta and Biedrins. The team's ability to remain a playoff team will also be an indicator of Mullin's job

Actually, I think that, by trading J-Rich, he lost some leverage in contract negotiations with Monta. Now Monta's the man at SG, and will demand to get paid as such. It would have been different if Monta had been signed before the trade.

migya wrote:Mullin will show how good he is with the level of contracts he gives to Monta and Biedrins. The team's ability to remain a playoff team will also be an indicator of Mullin's job

Actually, I think that, by trading J-Rich, he lost some leverage in contract negotiations with Monta. Now Monta's the man at SG, and will demand to get paid as such. It would have been different if Monta had been signed before the trade.

Actually, what trading JRich and starting Monta wil do is give Mullin a real indication of what Monta can do when given the full opportunity. Now Monta will have to show how good he is and thus how much money he should get paid

migya wrote:Mullin will show how good he is with the level of contracts he gives to Monta and Biedrins. The team's ability to remain a playoff team will also be an indicator of Mullin's job

Actually, I think that, by trading J-Rich, he lost some leverage in contract negotiations with Monta. Now Monta's the man at SG, and will demand to get paid as such. It would have been different if Monta had been signed before the trade.

Actually, what trading JRich and starting Monta wil do is give Mullin a real indication of what Monta can do when given the full opportunity. Now Monta will have to show how good he is and thus how much money he should get paid

migya wrote:Mullin will show how good he is with the level of contracts he gives to Monta and Biedrins. The team's ability to remain a playoff team will also be an indicator of Mullin's job

Actually, I think that, by trading J-Rich, he lost some leverage in contract negotiations with Monta. Now Monta's the man at SG, and will demand to get paid as such. It would have been different if Monta had been signed before the trade.

Actually, what trading JRich and starting Monta wil do is give Mullin a real indication of what Monta can do when given the full opportunity. Now Monta will have to show how good he is and thus how much money he should get paid

Ugh, as much as I hate agreeing with you, I do....

That is a great point.

Seems like you are not liking agreeing with anyone recently.

Thought you were on the right track not thinking like #32 but now you've lost me

migya wrote:Mullin will show how good he is with the level of contracts he gives to Monta and Biedrins. The team's ability to remain a playoff team will also be an indicator of Mullin's job

Actually, I think that, by trading J-Rich, he lost some leverage in contract negotiations with Monta. Now Monta's the man at SG, and will demand to get paid as such. It would have been different if Monta had been signed before the trade.

Actually, what trading JRich and starting Monta wil do is give Mullin a real indication of what Monta can do when given the full opportunity. Now Monta will have to show how good he is and thus how much money he should get paid

Ugh, as much as I hate agreeing with you, I do....

That is a great point.

Seems like you are not liking agreeing with anyone recently.

Thought you were on the right track not thinking like #32 but now you've lost me

migya wrote:Mullin will show how good he is with the level of contracts he gives to Monta and Biedrins. The team's ability to remain a playoff team will also be an indicator of Mullin's job

Actually, I think that, by trading J-Rich, he lost some leverage in contract negotiations with Monta. Now Monta's the man at SG, and will demand to get paid as such. It would have been different if Monta had been signed before the trade.

Actually, what trading JRich and starting Monta wil do is give Mullin a real indication of what Monta can do when given the full opportunity. Now Monta will have to show how good he is and thus how much money he should get paid

Ugh, as much as I hate agreeing with you, I do....

That is a great point.

Seems like you are not liking agreeing with anyone recently.

Thought you were on the right track not thinking like #32 but now you've lost me

migya wrote:Mullin will show how good he is with the level of contracts he gives to Monta and Biedrins. The team's ability to remain a playoff team will also be an indicator of Mullin's job

Actually, I think that, by trading J-Rich, he lost some leverage in contract negotiations with Monta. Now Monta's the man at SG, and will demand to get paid as such. It would have been different if Monta had been signed before the trade.

Actually, what trading JRich and starting Monta wil do is give Mullin a real indication of what Monta can do when given the full opportunity. Now Monta will have to show how good he is and thus how much money he should get paid

Ugh, as much as I hate agreeing with you, I do....

That is a great point.

Seems like you are not liking agreeing with anyone recently.

Thought you were on the right track not thinking like #32 but now you've lost me

migya wrote:Mullin will show how good he is with the level of contracts he gives to Monta and Biedrins. The team's ability to remain a playoff team will also be an indicator of Mullin's job

Actually, I think that, by trading J-Rich, he lost some leverage in contract negotiations with Monta. Now Monta's the man at SG, and will demand to get paid as such. It would have been different if Monta had been signed before the trade.

Actually, what trading JRich and starting Monta wil do is give Mullin a real indication of what Monta can do when given the full opportunity. Now Monta will have to show how good he is and thus how much money he should get paid

Ugh, as much as I hate agreeing with you, I do....

That is a great point.

Seems like you are not liking agreeing with anyone recently.

Thought you were on the right track not thinking like #32 but now you've lost me

migya wrote:Mullin will show how good he is with the level of contracts he gives to Monta and Biedrins. The team's ability to remain a playoff team will also be an indicator of Mullin's job

Actually, I think that, by trading J-Rich, he lost some leverage in contract negotiations with Monta. Now Monta's the man at SG, and will demand to get paid as such. It would have been different if Monta had been signed before the trade.

Actually, what trading JRich and starting Monta wil do is give Mullin a real indication of what Monta can do when given the full opportunity. Now Monta will have to show how good he is and thus how much money he should get paid

Ugh, as much as I hate agreeing with you, I do....

That is a great point.

Seems like you are not liking agreeing with anyone recently.

Thought you were on the right track not thinking like #32 but now you've lost me

migya wrote:Mullin will show how good he is with the level of contracts he gives to Monta and Biedrins. The team's ability to remain a playoff team will also be an indicator of Mullin's job

Actually, I think that, by trading J-Rich, he lost some leverage in contract negotiations with Monta. Now Monta's the man at SG, and will demand to get paid as such. It would have been different if Monta had been signed before the trade.

Actually, what trading JRich and starting Monta wil do is give Mullin a real indication of what Monta can do when given the full opportunity. Now Monta will have to show how good he is and thus how much money he should get paid

Ugh, as much as I hate agreeing with you, I do....

That is a great point.

Seems like you are not liking agreeing with anyone recently.

Thought you were on the right track not thinking like #32 but now you've lost me

migya wrote:Mullin will show how good he is with the level of contracts he gives to Monta and Biedrins. The team's ability to remain a playoff team will also be an indicator of Mullin's job

Actually, I think that, by trading J-Rich, he lost some leverage in contract negotiations with Monta. Now Monta's the man at SG, and will demand to get paid as such. It would have been different if Monta had been signed before the trade.

Actually, what trading JRich and starting Monta wil do is give Mullin a real indication of what Monta can do when given the full opportunity. Now Monta will have to show how good he is and thus how much money he should get paid

Ugh, as much as I hate agreeing with you, I do....

That is a great point.

Seems like you are not liking agreeing with anyone recently.

Thought you were on the right track not thinking like #32 but now you've lost me

I think its some sort of disease. Disagreeitis or something

Think there is a type of weed/herb that cures that

You gonna set me up...?

Unlikely,not nowadays but I'm sure you know someone that can

Uhhh, about five people.

Set by the ounce then

I love how in an hour and a half, we have gotten this far off topic...

migya wrote:Mullin will show how good he is with the level of contracts he gives to Monta and Biedrins. The team's ability to remain a playoff team will also be an indicator of Mullin's job

Actually, I think that, by trading J-Rich, he lost some leverage in contract negotiations with Monta. Now Monta's the man at SG, and will demand to get paid as such. It would have been different if Monta had been signed before the trade.

Actually, what trading JRich and starting Monta wil do is give Mullin a real indication of what Monta can do when given the full opportunity. Now Monta will have to show how good he is and thus how much money he should get paid

Ugh, as much as I hate agreeing with you, I do....

That is a great point.

Seems like you are not liking agreeing with anyone recently.

Thought you were on the right track not thinking like #32 but now you've lost me

I think its some sort of disease. Disagreeitis or something

Think there is a type of weed/herb that cures that

You gonna set me up...?

Unlikely,not nowadays but I'm sure you know someone that can

Uhhh, about five people.

Set by the ounce then

I love how in an hour and a half, we have gotten this far off topic...

migya wrote:Mullin will show how good he is with the level of contracts he gives to Monta and Biedrins. The team's ability to remain a playoff team will also be an indicator of Mullin's job

Actually, I think that, by trading J-Rich, he lost some leverage in contract negotiations with Monta. Now Monta's the man at SG, and will demand to get paid as such. It would have been different if Monta had been signed before the trade.

Actually, what trading JRich and starting Monta wil do is give Mullin a real indication of what Monta can do when given the full opportunity. Now Monta will have to show how good he is and thus how much money he should get paid

Ugh, as much as I hate agreeing with you, I do....

That is a great point.

Seems like you are not liking agreeing with anyone recently.

Thought you were on the right track not thinking like #32 but now you've lost me

I think its some sort of disease. Disagreeitis or something

Think there is a type of weed/herb that cures that

You gonna set me up...?

Unlikely,not nowadays but I'm sure you know someone that can

Uhhh, about five people.

Set by the ounce then

I love how in an hour and a half, we have gotten this far off topic...